


All in all, it's just a hole in the wall!

by troubleseeker



Series: kinktober 2018 [29]
Category: Supernatural
Genre: Bottom Sam Winchester, Coffee, Condoms, First Time, Glory Hole, Kinktober 2018, M/M, Masturbation, Oral Sex, Prostitute Sam Winchester, Prostitution, Protective Dean Winchester, Safe Sane and Consensual, Sleepy Sex, Top Castiel, Top Dean Winchester, face fucking, pimp dean, public, safe sex
Language: English
Status: Completed
Published: 2018-12-04
Updated: 2018-12-04
Packaged: 2019-09-07 12:52:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,295
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16854301
Author URL: https://archiveofourown.org/users/troubleseeker/pseuds/troubleseeker
Summary: kinktober day 29 -Glory hole |Double (Or more) Penetration| Sleepy Sex |MassageIt takes a lot of money to keep the Winchesters moving around like they do, and why not cash in on Sam's oral fixation? Glory holes are a plentyful resource scattered through the entirety of the US, and Sam's knees have seen plenty of them. We join him (and his bodyguard/pimp/brother) at the end of a long shift.





	All in all, it's just a hole in the wall!

Not everyone would feel safe kneeling in a dingy bathroom stall. Mouth to the wall and sucking anything and everything came through a hole worn smooth over years of use with nothing but an old sweater protecting their knees.

Most people would feel fear, or guilt ... or both. Probably a healthy helping of shame thrown on top. Not Sam though, he wasn't just  _ anyone _ . 

He could kneel here for hours. And, sure, he'd feel plenty of stuff, but it wouldn't be fear, or guilt, or shame. Those emotions were reserved for situations that deserved them. This was just a job. Most days, it was even a fun job!

He did get tired though. With the sun long gone, and just a dusty bulb on a string to cast shadows around their chosen hideaway; the hours weighed down on him. 

Made him wish for his bed.

“Sure you can fuck his throat. Five extra, though.”

Sam swayed from side to side a bit, eyes closed as he sipped from the thermos he’d thought to bring along this time. No central heating of any kind in public bathrooms. Not in any  _ he'd _ seen anyway, and he’d seen plenty. Not in this one either; tucked away where it was at the edge of a park. Sitting nearly still, anyone would get cold. Coffee kept him warm from the inside out, and while he’d gotten used to the taste of latex fucking ages ago, it wasn’t ever going to be his favourite. Plus, no one wanted a blowjob where the guy on his knees kept pausing to yawn.

So yeah. Coffee helped. It didn’t keep helping forever. But it helped.

“Nose to the wall baby!”

Sam nodded, not that Dean could see him. The cap of his thermos clinked as he screwed it on, loud in the confines of the stall. It wasn’t locked. Didn’t have to be. If anyone even tried to do something stupid, Dean would have them out the building faster than you could blink.

He still had his gun with him just in case.

Sam got back into place just as the newest dick inched its way through the wall. Already wrapped up all nice and pretty. Looked clean too. Sam let his fingers do the walking first. Checking for holes or tears, and then further up for things he didn’t want to mess with.

Sure, Dean handed everyone a condom when they walked through the door and paid him, but that didn’t mean his brother got down to inspect people’s dicks with a fine tooth comb. That was Sam’s job. 

Whoever this was, he smelled nice, shaved down here at least.

The guy hummed impatiently, and good customer service was important so Sam sucked him in. Heavy on his tongue, he tested the size of the prick against his cheek before he let it further back. 

He’d seen and sucked pretty much every kind of dick out there - most remained anonymous - and while there were a couple of outliers most were average. Big enough to get deep enough to tickle his gag-reflex but nothing compared to what porn would have people believe. This one wasn’t any different. 

There were two drawer handles screwed into the wall. Mismatched and probably barely older than the hole itself. But if he held on to them he could keep his head pretty still. 

Bobbing a couple more times, Sam opened up his throat and took the guy deep. Nose to the wall.

The guy groaned, fist slamming against the divider; rattling the entire rickety construction. Sam held on to the handles, eyes closed, and let the guy fuck him. 

Every couple of thrusts he'd have to fight his gag reflex a bit. He let the guy feel it though. The way his throat flexed around the intruder made most dudes happy. 

Yeah. Guys usually liked feeling how they choked him. Made ‘em feel big ‘n strong.

They'd be less proud of their dick if he puked all over it though. So Sam kept to that golden middle ground that had him gag but not retch. 

A + customer service, five stars, and a feather in his cap.

“He can take harder than that, dude. Use his mouth.”

Sam rolled his eyes. Most of his customers kept their mouths shut. Sure, he got a bit of groaning and some said thank you. But few wanted to have a conversation while they got their dick sucked in a public bathroom. Dean however, rarely shut up.

Couldn’t just let their customers have their fun without having to perform for an audience, could he? 

Buckling to peer pressure, the guy sped up, and Sam didn’t care one bit. All he had to do was tighten his grip on the handles to make sure his head stayed in place. 

If they had college courses in blowjobs, he’d have a fucking PhD. 

His arms ached a bit by the time the guy came down his throat …. Well, into the condom. But the condom was on his dick, and said dick was as deep as it could go, so semantics aside Sam was being a good boy.

He hummed, relishing the little yelped curse on the other side of the panel. 

“He’s good ain’t he?” Dean drawled from his spot by the door. Sam could construct the image without peeking through his hole. 

Dean liked to take up more space than he needed in situations like this. Leaning against a wall, or sitting in a stool, he spread his legs wide on purpose. Didn’t do that shit in their rooms; in private. Just when they were working. Munching casually on some kind of junk food. Chips, chocolate, pretzels … lollipops that made Sam want to kiss him silly. Didn’t matter, it was a clear message. 

I know what I’m doing. Don’t try to pull one over on me. Don’t try to hurt him. I’ll end you.

Sam pulled the condom off, tying a quick knot before dropping it in the trash can that probably wouldn’t be emptied for weeks. The guy pulled back, and Sam let his attention drift back to his coffee, and stifling his yawns.

Yawning was up there with puking on someone’s dick. At least the first one meant you were whoa big …  but yawning? That was rarely a good thing. 

“Yeah_ uh. He’s good. Thanks.”

Dean laughed around the handful of chips he’d shoved in his mouth. Sam had heard the krinkle of the bag all evening, but Dean didn’t have any coffee so neither of them could complain much.

“See you around, man. He’s here again tomorrow night.”

Sam shifted his weight a bit. Word of mouth was really the only way they had to advertise their pop-up shop since they moved so often. On one hand, they probably missed out on the people who only heard about them after they left. But being the newest fuck in town did pull in a lot of people who just wanted something fresh.

Either way. They made plenty.

Plenty to pay for their rooms, food, guns, and gas. Baby had been pampered ever since they started up this side business. 

“‘Nother one comin your way baby.”

Sam didn’t look at his watch. There was no point in knowing how long he’d already been here. The only thing that mattered was the cash they were forking over to Dean.

The dick that poked its way in didn’t have a condom on yet. Sam sighed. Sure, it looked clean, but no way in hell was he sucking a dick he didn’t know bare.

“Sorry man. No glove no love.”

He wasn’t being loud, but Sam caught the distinct lack of chewing noises echoing through the building. The person attached to the potentially diseased dick stuck to a whisper, like Dean couldn’t hear him from ten feet away.

“Come on. I’m clean.”

Ugh. He was too tired for this song and dance.

“Rules are rules. Put on your raincoat and I’ll make you feel good, or no deal.”

“What if I give you like five bucks extra?”

Sure. Sure! Five bucks would totally cover the costs of getting his blood work done.

“No can do buddy.”

“It’s just. I don’t like condoms.”

“Uhuh.”

“They’re too small.”

Sam practically saw his own brain with how hard his eyes rolled.

“ _ Uhuh _ . Listen here man. I’ve seen a lot of dicks, and I’m not gonna lie … you’re not that big.”

There was a lot of indignant spluttering, but Sam didn’t waste good customer service on douchebags. This one would either get over himself and get what he paid for wearing his complimentary helmet, or he’d have to leave. Sam raised his hand to give Dean the signal knock when the guy pulled back. 

“Better be fucking worth it.”

Sam took twice as long inspecting the condom. He’d had weirdos messing with their protection before. 

“I’ll do my very best.”

It was quick. So quick, it would have probably have been pathetic had he managed to talk Sam into going bare. Sam tied the condom off, reaching for his thermos in the same move. 

“Hope you had fun, byby now.”

The slap of Dean’s palm on the guy’s back echoed around the room, and Sam was glad to not hear Dean invite this one back. Wasn’t worth the money.

“You still good, baby?”

No names was a base rule, but Sam loved hearing nicknames all night. He yawned silently. If Dean was asking, it meant there was at least one more guy standing ready to pay for the privilege to get in his mouth.

“Sure.”

They wouldn’t be here much longer, the case was pretty much done … he could sleep out tomorrow.

“Okidoki! Go on in.”

Sam worked his jaw a bit, waiting for the next dick pull up into the station.

“Hi, uh. This is my first time. So uh_ do I just?”

Dean would have checked the guy’s ID, but he sounded young. They’d walked this walk before.

“Take your time, man. Ever put a condom on before?”

“Um. Yeah. Just to see how it worked. Didn’t wanna fumble if I ever got the chance to_ you know.”

Sam hummed.

“So do that again. Get yourself nice ‘n hard and roll the condom on.”

There was a clink of a belt, a zipper, clothes moving around and then skin on skin. No wrapper yet.

“Are you hard?”

The kid froze.

“Not all the way. I’m sorry. I’ve never... I haven’t … I should leave, shouldn’t I?”

“Nonono. Don’t worry. It’s your first time, man. Need to learn how to get your dick sucked one way or another. Just stroke yourself a bit. This is meant to feel good.”

Sam peeked through the hole to see lightly tanned hands jerking at what looked to be his best dick of the night.

“There you go. Get it all ready for me.”

Mystery man groaned, and Sam was happy to see that his hands were gaining confidence. 

“That’s a nice looking dick you’ve got there by the way. Lucky me.” Sam crowed.

“Really? You’re not just saying that?”

Sam didn’t often say anything at all when it came to his Johns.

“No reason to lie, sweetheart. I’d give you a hand if there wasn’t a wall in the way. Gonna make someone very happy with that one day, dude.”

The man huffed.

“No one calls me that, it’s like you’re talking to my older brother.”

“I can call you whatever you want. You’re in charge here.”

“Yeah, I had to pay they guy at the door, and he could probably snap me in half … so.”

The kid had a sense of humor, Sam laughed.

“You can ignore him, man.”

Sam watched as the guy’s dick started obeying the laws of stimulation. Oh yeah, looked good. Thicker than most, and if he was a grower plenty to work with.

“Just call me Cas. That’s what most people do.”

Probably short for something, or a nickname. Not that Sam was one to judge, or care, really.

“Well, Cas. I like the look of your dick. Can’t wait to suck it like a lollipop.”

And there it was. Some guys just needed a personal touch. Cas was plenty hard to roll a condom on, even if he wasn’t all the way there yet. Sam would take care of the rest.

“Now take out the condom and slide it right down. Which flavour did you get?”

Dean switched them up a bit, but Sam did have his favourites.

“Cherry.”

Bingo. 

“That’s my favorite! Come on. Let me have it, Cas. Come on. Want it. Want you.”

There was a finesse to putting on a condom. It took most guys a bit of practice to get it right, or at least do it smoothly and quickly. Cas was a newbie. Sam licked his lips as he watched the kid fumble in his haste.

“Fuck you look good. Can’t believe no one’s jumped that yet.”

He was pretty sure Cas was blushing now, there was a strip of skin visible above his undone slacks, and Sam stared at it through his peephole; definitely pinker than at the start.

“I can’t really tell people I’m into guys.”

Aah. Closeted and hungry. 

“My condolences, now let me suck your dick.”

Cas laughed, and Sam was glad. First times were nerve wracking enough, let alone with a perfect stranger hidden behind a wall.

“Do I just?”

“Just slip it right in, I’ll take it from here. You can put your hands on the wall if you like, cause I’m about to blow your mind.”

“I don’t doubt tha_ oh!”

He’d seen Cas put the condom on, but they could tear if handled wrong and Sam as more on the safe than the sorry side of strangerfucking. He held Cas’s dick carefully, checking as he stroked the latex further up. 

The rush of blood was palpable, Cas’s dick plumping up firmer by the second he was holding him.

“Just making sure everyone’s safe.” Sam elaborated. If this was the kid’s first sexual experience he might as well learn more than just how good it felt to have someone’s mouth on your dick. “Looking good. But better safe than sorry, you know?”

Cas said something, mostly guttural, probably affirmative.

“And when I’m done checking you can have my mouth, cause that’s what you want, isn’t it?”

Tiny thuds, way up high. Cas was nodding against the wall, and Dean was the one who finally goaded Sam into action.

“Enough teasing baby. Show him how it’s done before he faints.”

Sam went slow. This guy would be the last one he served tonight, so he might as well savour it. Plus, cherry!

Pursed lips kissed the tip of the kid’s dick. Once. Twice. And then slipped further down to the sound of a dying animal. Damn the kid was vocal.

One hand holding the first impressive dick he’d seen all week steady, Sam paid attention to the bulbous head first. Slow sucking pressure then off again, back to light kisses, and when he heard Cas take at least one deep breath, back down again. 

Acclimatizing the kid’s dick to his mouth before he went fancier. 

Sure, he could deepthroat and finish Cas off in seconds, but that wouldn’t do that many good things to the kid’s ego. Less was more here, especially if he kept moaning like that. With only about half his customers bothering to pause for a thank you, this was doing amazing things to  _ his _ confidence.

Another easing minute of moans and shudders later, Sam found that he was getting hard too. And he  _ did _ have one hand free …

After hours on his knees fueled by not much more than coffee, it was time to get something better than caffeine in his system. Sam shifted, dick free in a matter of seconds. 

He pulled back to hear Cas whimper, and spit on his hand.

It was a bit on the colder side, but he ignored the mild discomfort to moan around the fat dick in his mouth. God he loved sucking dudes off. 

Something about the stretch in his jaw, the stretch in his throat, the way his tongue got tired. Mmmm. Perfect.

“Oh fuck. Oh fuck. Oh fuck.”

Sam grinned, backing off for a full three seconds before deepthroating. Cas  _ definitely _ tickled his gag reflex, but Sam suppressed it. Instead, he swallowed; the muscles in his throat clamping down on Cas’s head. Sacharine sweet artificial cherry drooling down his chin as he held.

“Oh God. Please.”

Sam had pulled back completely, stroking the spit slick latex while Cas found his bearings. 

“Wouldn’t want this to be done too quickly, would you?” His voice was going scratchy, which said something about the other guys.

“Nuh_ I_uh _I don’t know.”

Sam paused the hand on Cas’s dick, speeding up on his own.

“You hear that?”

Cas was breathing hard, so he might actually not hear anything. But he caught his breath, dick twitching in Sam’s grasp.

“Are_ Are you?”

He had to bite back a laugh. The kid sounded scandalized, or at least surprised.

“Yeah, Cas.” He couldn’t resist a couple of kisses. “Got me all horny with the way you moan for me.”

Cas whimpered. “I don’t_ fuck, that’s so good.”

“No need to think, Cas. Just let me make you feel good.”

Cas nodded - Sam could hear the slide of his head against the wall again - breathy little  _ yeah yes, yes’s  _ echoing around the room next to the filthy slap of skin on skin. He was close enough, so Sam got back to work. 

Did he let the kid come first? Or did he? 

Deciding to go with the flow, Sam swirled his tongue across the skin pumping across his lips. He doubted the kid had suddenly grown in confidence. Most likely, some kind of primal urge was taking over. 

Not that Sam would ever disagree. There was pleasure to be had, why not take it? Moans rising to a crescendo, Sam pushed forward just as Cas did, letting the kid grind deep as he came. Throat relaxed, he let himself fall over the edge too. With Cas moaning loud enough to drown out everything else he didn't have to play it up.

Sam looked down past Cas's dick - still in his mouth, of course. customer service and oral fixations went well together in this line of work - at the messy drip of his own come down the wall, and reminded himself to at least wipe that down before they left. If only because he'd be here again tommorrow.

Gently. Slowly. Easy. Sam backed up, planting goodby kisses all over Cas’s dick before stripping off the condom and dropping it on top of the pile with its buddies.

Cas was dazed, fumbling to put his dick away one handed, leaning against the groaning divider for support. Sam watched him through the hole, content with his day's work.

“You good, Cas?”

Cas hummed dreamily, and Sam was about to get up and stretch his legs when Dean called out.

“You ready for one more, baby”

“Ugh. C'mon man. I just came. ‘M tired”.”

“Exactly. No, no man. I'm not kicking you out after that show! Sit down. You can watch.”

Sam knew exactly what was coming. He leaned back, and Dean’s dick pressed through the hole, bare and so fucking hard it made Sam’s dick twitch again.

“You think I’m going to stand there listening to you jerk off to the best dick you’ve ever sucked -  _ apparently  _ \- and not wanna get involved. Fuck you.”

Sam laughed - full belly giggle - as he was getting his clothes back in order, cheek rubbing against his big brother's dick.

“You jealous?”

“Just get my dick wet!”

**Author's Note:**

> If you want to come yell at me on [tumblr](http://ryugarika.tumblr.com/) ... feel free to, I can take it.
> 
> Comments feed me!
> 
> Check back tomorrow, for ... gagging and swallowing! Some dub-con clouds but everyone's happy! (and that's all that matters, right?)


End file.
